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Not generally a fan of matchy names anyway, but if you didn't match them the first time, it might seem weird if you do the second. (and the same vice versa, if the first set matched, it would be weird not to match the second set)

Go with what you like. I would not try to "match" their names in an obvious way (close-sounding names, like Kerry & Kelly, Joan & Jane, etc.) but I wouldn't reject names just because they might begin with the same letter. I think names can be distinct & different from each other even if they begin with the same letter.
We actually considered the names Ambrose & Anselm for our twin sons, not to "match" them with two "A names" but because they were two names that had some meaning for us. (Two monks who had been important to my husband at his boarding school and remain in his life, as well as names we like.) It wouldn't have been about matching, but choosing two strong individual names. In the end, we just weren't inspired to do it but we considered it.
Sometimes, two names you like start with the same letter, even when it's not a set of same-age siblings. If they're individual names, not simply cutesy matches, why not??